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Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13735-9. doi: 10.1002/anie.201307250. Epub 2013 Nov 7.

One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China).

Abstract

All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.

KEYWORDS:

asymmetric catalysis; heterocycles; organocatalysis; spiro compounds; synthetic methods

PMID:
24346948
DOI:
10.1002/anie.201307250
[Indexed for MEDLINE]
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